10 Lessons I’ve Learned in 10 Years of Entrepreneurship

In the blink of an eye, ten years have passed since starting Oh Yes. What started as an accidental journey of entrepreneurship has turned into a full-fledged marketing agency with a lot of lessons learned along the way. In hindsight, I’m proud of the twenty-six year old young woman who had the audacity to believe she could do this. Thirty-six year old Kathy is better for every high and low along the way. 

In no particular order, here are the top 10 lessons I’ve learned as an entrepreneur:

1. Systemize and Document EVERYTHING!

If all the caps and exclamation points didn’t give it away, if you take nothing else from this blog, let this be the one you do! As a service-based business, our intellectual property and the internal team that helps implement the work is the lifeblood of attracting and retaining clients that turn into raving fans. The reality though, is that team members come and go, which means that training and mentoring is a constant part of your role as a business owner. Unfortunately, this is one of those lessons I learned the hard way when integral team members moved on. Now, we make sure to document our processes, any nuances or preferences by client, and we integrate it into our agency tools to make it a seamless experience for all. The team is more autonomous, we’re able to spot inefficiencies, mistakes decrease, and our clients receive maximum value and support. It’s a win across the board for all!

2. Delegation is the only way to scale.

Allow me to ruffle some feathers: your business is not “your baby” and you may not be the most qualified (or best) person to do every task anymore. In fact, if you’re hiring well– your team is probably better at their role than you are, and that’s a good thing! I know, I know– that was a bit direct, but if you’re anything like me, we often don’t hear things until they’re said very matter of factly. I had the opportunity to be a part of the Goldman Sachs 10k Small Businesses program in early 2023 and during this 16-week MBA-like intensive, they challenged and dissected every part of my business. It was humbling and eye-opening, and also made one thing very clear: our gifts and talents, and the team and process we assemble to deliver this service, is how we serve our clientele. Let me repeat that: what we’re great at and our unique approach to delivering that is how we HELP others. I don’t know about you, but that blew my mind. Up until that point I hadn’t seen our services as serving. Now I do, and I’m on fire to delegate so we can elevate and scale. Helping small businesses thrive through messaging, marketing and branding is how we’re providing transformations!

3. A CEOs job is to problem-solve, uphold a standard of excellence and cast a vision.

If you’ve been in any position of leadership in your life, you’ll likely relate to the following statement: The hardest part of a job is the people. The most rewarding part of a job are the people. Truth be told, being the captain of this ship is a lot like looking into a mirror daily. It has shown me my areas of growth, where I’ve missed the mark, and the strengths I bring to the team. Going a layer deeper, it’s also an enormous responsibility ensuring that the company and team are working efficiently to run a profitable business, maintaining excellence in service (always), and supporting the client and team well. Leadership, as I’ve learned, is a verb. It requires complete accountability and a commitment to integrity. When I accepted that my role was to problem-solve when needed, address quality issues early and fast without hesitation, and cast a vision the team could get behind– it started making more sense where I fit in.

4. Clear and proactive communication goes a long way.

Not all companies are made equal. Clear and proactive communication is the unsung hero of keeping projects on track and teams on the same page. In any service-based client relationship, a less obvious part of what we do is put our clients’ minds at ease and nothing throws up red flags faster than poor communication. Have a tight timeline and need to keep the train on track? Communicate! Running into issues and sensing frustration? Communicate! Noticing approval turnaround time is starting to lag? Communicate! Consistency in this area is the magic sauce and it allows you to work through almost any situation with grace and kindness.

5. Develop your signature framework.

This “lesson learned” is in my top three, for sure! Unfortunately, it’s also something that requires lived-experience and proven results in order to really hold weight. But that doesn’t mean that your hands are tied and no progress can be made in the process. If I knew then what I know now, I would have taken more detailed notes about what worked, kept better track of what a successful client onboarding experience looked like, and what timeless marketing principles added value time and time again. Having a signature framework takes you from novice to expert in many ways and shows the intentionality with which you approach your craft. Secondary benefits include confidence-boosting for the team, developing efficiencies as a business and knowing your threshold to add new clients while not sacrificing value.

6. You’re probably not thinking big enough.

I’m not much for “woo” content but I do believe in the power of personal development and intention in your life. Outside of marriage and motherhood, entrepreneurship has been an exceptional “life school” experience that continues to refine and challenge me in each new season. Here’s what I want you to know: the opportunities you’re landing are a direct reflection of your mindset, self-worth and self-talk. Some seasons are for growing the business and other seasons are for maintaining the business (hello, deployments and postpartum months!), but in ALL of those seasons, seeking out personal growth and sharpening your skills is a must. I recently completed the 75 Hard Mental Resilience program (highly recommend it!), and the inconvenience of it all required a new level of focus and boundaries. The physical benefits were great, the mental resilience built was pivotal, and the close to $100k in business closed in 10 weeks showed me, yet again, I was not thinking big enough. These days, I aim to be the most entry-level person in the room. I try to be a sponge and have discernment when it comes to knowing what to apply to my personal and professional world.

7. Boundaries create sustainability.

This point goes hand-in-hand with the one above. Your ability to have good boundaries is tied to what you believe you’re worthy of and how self-aware you’re willing to be. Boundaries are also incredibly important for the longevity and sustainability of the business you’re building. And here’s the thing– YOU get to decide what those boundaries are and when they’re permeable and when they’re not. Client-work can become all-consuming and it’s so very easy to start working late at night, on the weekends, answering after-hours phone calls, and so on and so forth. But remember, your business is NOT your identity and it should not be your entire life’s work. There’s likely a big world and a handful of people who’d love your presence at-home, not just in body but in mind and spirit. “Be present where your feet are” is an audible I tell myself (my kids, my team, my friends) often. Ask for feedback from those you trust to see how you’re doing in this department. Know your boundaries, hold them firm, and know when to remove clients or team members that repeatedly disrespect them.

8. Avoid shortcuts. Invest early and often.

In the beginning, it’s common to fulfill just about every role in your company while making sure to stretch each dollar. But eventually, it’s time to invest early and often. Shortcuts feel, well, like shortcuts!  You can find great options to help you navigate everything from HR to accounting at every price point and sometimes, you may even need to invest in something beyond your comfort level to elevate your operations and expertise. Better to do this early and often, than reactively and in catch up mode.

9. It’s deeper than the work.

This one can put me in tears pretty quickly. Oh Yes is bigger than the work. It’s about the impact and lessons learned we’re experiencing through the people we get to do life with. In my 10 years at Oh Yes, I’ve walked through divorces, miscarriages, weddings, cancer diagnosis, new babies, a client’s daughters getting struck by lightning while hiking, selling and dissolving businesses, promotions, pandemics (hello!), and so much more. Our value on collaboration and being a person of character means we show up when conditions are less than ideal and we become an extension of our peoples’ community. The work we do is a daily opportunity to leave encounters, relationships and the world better than we found it– whatever that looks like day-to-day.

10. Curiosity trumps being correct.

This one has become a bit of a life mantra in the passing years. When you get the opportunity to work with different people who see the world differently than you, it’s important to keep an open mind to what could be. Sometimes, the answers seem pretty black and white, but leading with curiosity leaves room for something unforeseen to come forth. Negotiation, skillful communication, checking egos at the door are all an important part of this process. The result? Creative friction that leads to a better plan and final product. Stay curious my friends!

Oh Yes Communications is a clarity-driven marketing agency that specializes in messaging, branding, and creative services. Our mission is to elevate every brand and business to reach their full potential.

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